Synthesis and crystal structure of catena-poly[[di­bromido­zinc(II)]-μ-2,3-di­methyl­pyrazine-κ2N1:N4]

Näther, C.; Bhosekar, G.

doi:10.1107/S2056989025007613

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Volume 81| Part 10| October 2025| Pages 928-931

https://doi.org/10.1107/S2056989025007613

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Synthesis and crystal structure of catena-poly[[dibromidozinc(II)]-μ-2,3-dimethylpyrazine-κ²N¹:N⁴]

Christian Näther ^a ^* and Gaurav Bhosekar ^b

^aInstitut für Anorganische Chemie, Universität Kiel, Max-Eyth.-Str. 2, 24118 Kiel, Germany, and ^bSuman Ramesh Tulsiani Technical Campus - Faculty of Engineering, Pune, India
^*Correspondence e-mail: [email protected]

Edited by X. Hao, Institute of Chemistry, Chinese Academy of Sciences (Received 20 August 2025; accepted 25 August 2025; online 5 September 2025)

The title compound, [ZnBr₂(C₆H₈N₂)₂]_n, was prepared by the reaction of zinc bromide with 2,3-dimethylpyrazine in acetonitrile and is isotypic to the corresponding compound with zinc chloride reported recently [Näther & Bhosekar (2025 ). Acta Cryst. E4, 813–820]. The asymmetric unit consists of one zinc cation, two crystallographically independent bromide anions and one 2,3-dimethylpyrazine ligand, all of which are located in general positions. In the crystal, the Zn cations are tetrahedrally coordinated by two bromide anions and two 2,3-dimethylpyrazine ligands and are linked by bridging 2,3-dimethylpyrazine ligands into corrugated chains that proceed along the c-axis direction. Measurements using powder X-ray diffraction show that a pure crystalline phase was obtained.

Keywords: crystal structure; coordination polymer; synthesis; zinc bromide; 2,3-dimethylpyrazine.

CCDC reference: 2482737

1. Chemical context

We have been interested in the synthesis and structures of transition-metal halide and pseudo halide compounds with N-donor coligands for a very long time because they show a versatile coordination and structural behavior. This is especially the case for compounds based on Cu^I, in which the metal cations forms mono or dinuclear complexes or they are linked by the halide or pseudo halide anions into one-dimensional or two-dimensional networks (Näther et al., 2001 , 2002 ; Kromp & Sheldrick, 1999 ; Peng et al., 2010 ; Li et al., 2005 ). In most cases, for a given copper(I) halide or pseudo halide and a given coligand, compounds of different stoichiometry are observed, which include coligand-rich and coligand-deficient compounds. In this context we have found that the coligand-rich compounds can be transformed into the corresponding coligand-deficient compounds by heating (Näther & Jess, 2002 , 2004 ).

In contrast to copper(I), compounds with twofold positively charged cations such as, for example, Zn^II or Cd^II, show a limited number of MX₂ networks (M = Zn, Cd). In these structures a tetrahedral and also an octahedral coordination can be observed. The former coordination dominates for Zn^II, whereas the latter is frequently found for Cd^II (Neumann et al., 2018a ,b ). For Zn^II mainly discrete complexes are observed, whereas for Cd^II examples are known in which the metal cations are linked into chains (Neumann et al., 2018a,b). The MX₂ complexes or chains can additionally be connected if bridging coligands like pyrazine are used, and several such compounds are reported in the literature (Bailey & Pennington, 1997 ; Pickardt & Staub, 1997 ; Bhosekar et al., 2006 ; Bourne et al., 2001 ; Song et al., 2004 ). Based on these observations, we prepared new ZnCl₂ compounds with 2,3-dimethylpyrazine as ligand with the composition ZnCl₂(2,3-dimethylpyrazine) and ZnCl₂(2,3-dimethylpyrazine)₂ (Näther & Bhosekar, 2025). In both compounds the Zn cations are tetrahedrally coordinated, leading to the formation of discrete complexes in the 2,3-dimethylpyrazine-rich compound, whereas in the 2,3-dimethylpyrazine-deficient compounds the Zn cations are linked into chains. Very recently a corresponding compound with the composition ZnBr₂(2,3-dimethylpyrazine)₂ was reported that is isotypic to ZnCl₂(2,3-dimethylpyrazine)₂ and which was investigated for its photophysical properties (Yang et al., 2025 ). Based on these results, we assumed that a further compound with ZnBr₂ with the composition ZnBr₂(2,3-dimethylpyrazine) could be prepared that might be isotypic to its ZnCl₂ analog. Therefore, zinc bromide was reacted with equivalent amounts of 2,3-dimethylpyrazine and the crystals obtained were characterized by X-ray single crystal and powder diffraction.

2. Structural commentary

The new compound ZnBr₂(2,3-dimethylpyrazine) is isotypic to the corresponding chloride compound ZnCl₂(2,3-dimethylpyrazine) reported recently (Näther & Bhosekar, 2025). The asymmetric unit of the title compound consists of one Zn cation, two crystallographically independent bromide anions and one crystallographically independent 2,3-dimethylpyrazine ligand in general positions (Fig. 1). The Zn cations are fourfold coordinated by two N atoms of the 2,3-dimethylpyrazine coligands and two bromide anions in a distorted tetrahedral geometry. The N—Zn—Br angles deviate only slightly from the ideal tetrahedral values, whereas the Br—Zn—Br angles are larger and the N—Zn—N angles are smaller (Table 1), presumably because of steric repulsion between the halide anions. The metal cations are linked into chains along the crystallographic c-axis direction by bridging 2,3-dimethylpyrazine ligands (Fig. 2). These chains are corrugated because of the tetrahedral coordination (Fig. 2).

Table 1
Selected geometric parameters (Å, °)

Zn1—N2ⁱ	2.085 (6)	Zn1—Br1	2.3380 (12)
Zn1—N1	2.118 (7)	Zn1—Br2	2.3501 (12)

N2ⁱ—Zn1—N1	103.1 (3)	N2ⁱ—Zn1—Br2	115.18 (19)
N2ⁱ—Zn1—Br1	109.2 (2)	N1—Zn1—Br2	108.13 (19)
N1—Zn1—Br1	105.25 (19)	Br1—Zn1—Br2	114.87 (5)
Symmetry code: (i) $[-x+y+1, -x+1, z-{\script{1\over 3}}]$ .

Figure 1
Crystal structure of the title compound with atom labeling and displacement ellipsoids drawn at the 50% probability level. Symmetry code for the generation of equivalent atoms: (i) −x + y + 1, −x + 1, z − $[{1\over 3}]$ .

Figure 2
Fragment of the extended structure of the title compound with a view of part of a chain and intrachain C⋯H—Br hydrogen bonding shown as dashed lines.

3. Supramolecular features

In the crystal, intrachain C—H⋯Br hydrogen bonding with C—H⋯Br angles of 151 and 150° is observed (Fig. 2 and Table 2). These chains are linked by interchain C—H⋯Br contacts that show much smaller angles and thus should represent only very weak interactions (Fig. 3 and Table 2).

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Br1ⁱⁱ	0.94	2.95	3.604 (8)	128
C3—H3⋯Br2ⁱⁱⁱ	0.94	2.99	3.687 (8)	132
C4—H4⋯Br2	0.94	2.95	3.605 (8)	128
C5—H5C⋯Br1	0.97	2.95	3.824 (10)	151
C6—H6A⋯Br1^iv	0.97	2.99	3.710 (10)	132
C6—H6C⋯Br2ⁱⁱ	0.97	2.95	3.820 (10)	150
Symmetry codes: (ii) $[-y+1, x-y, z+{\script{1\over 3}}]$ ; (iii) $[-y+2, x-y+1, z+{\script{1\over 3}}]$ ; (iv) $[-y+1, x-y-1, z+{\script{1\over 3}}]$ .

Figure 3
Crystal structure of the title compound with a view along the crystallographic a-axis direction and intrachain C⋯H—Br hydrogen bonding shown as dashed lines.

4. Database survey

As mentioned above, the title compound is isotypic to the corresponding 2,3-dimethylpyrazine compound with ZnCl₂ already reported in the literature (Näther & Bhosekar, 2025). There are two additional compounds with the composition ZnCl₂(2,3-dimethylpyrazine) (Näther & Bhosekar, 2025) and ZnBr₂(2,3-dimethylpyrazine) (Yang et al., 2025) that are isotypic and that are built up of discrete complexes with a tetrahedral Zn coordination. Further compounds with twofold positively charged transition-metal halides and 2,3-dimethylpyrazine as ligand are not reported in the CCDC database (CSD Version 5.43, January 2025; Groom et al., 2016 ) using CONQUEST (Bruno et al., 2002 ). However, some compounds are known with the unsubstituted ligand pyrazine. These include CdX₂(pyrazine) [X = Cl, Refcode TISSUJ ( (Pickardt & Staub, 1997)] ), X = Br, RINSIQ and RINSOW (Bailey & Pennington, 1997); X = I, RINSIQ01 and RINSOW01 (Pickardt & Staub, 1997)] in which the metal cations are octahedrally coordinated and are linked by pairs of halide anions into chains that are further connected into layers by the pyrazine ligands.

More compounds are reported with Zn^II cations and pyrazine. In contrast to the title compound with 2,3-dimethylpyrazine as coligand, these compounds show an octahedral coordination. This is the case in, e.g., ZnCl₂(pyrazine)₂ (Refcode REMPAB; Bhosekar et al., 2006) in which the Zn cations are linked into layers by the pyrazine ligands. In the pyrazine-deficient compound ZnCl₂(pyrazine) (Refcode TISTAQ; Pickardt & Staub, 1997), the Zn cations are linked into chains by pairs of bridging chloride anions that are further connected into layers by the pyrazine ligands. With ZnBr₂, two compounds are known of which the pyrazine-rich compound ZnBr₂(pyrazine)₂ crystallizes in two modifications with layered networks of the same topology. One of them is isotypic to the corresponding chloride compound [Refcodes EBOLAI (Bourne et al., 2001) and EBOLAI01 (Bhosekar et al., 2006)]. They also include ZnBr₂(pyrazine), which crystallizes differently from the chloride compound (Refcode EBOKUB; Bourne et al., 2001). Finally, ZnI₂(pyrazine) is reported that shows a structure similar to that of the bromide compound [Refcodes ISOPOV (Song et al., 2004) and ISOPOV01 (Bhosekar et al., 2006)].

5. Synthesis and crystallization

Zinc bromide and 2,3-dimethylpyrazine were purchased from Sigma-Aldrich.

Synthesis

0.5 mmol (112.6 mg) of zinc bromide were reacted with 0.5 mmol (54.1 mg) of 2,3-dimethylpyrazine in 1 mL of acetonitrile. The reaction mixture was stirred for 3 d and the precipitate was filtered off and dried. Single crystals were obtained using the same ratio of reactants without stirring.

The title compound was additionally investigated by X-ray powder diffraction, which shows that a pure sample has been obtained (Fig. 4).

Figure 4
Experimental (top) and calculated (bottom) X-ray powder pattern of the title compound.

Experimental details

The PXRD measurements were performed with Cu Kα₁ radiation (λ = 1.540598 Å) using a Stoe Transmission Powder Diffraction System (STADI P) that is equipped with a MYTHEN 1K detector and a Johansson-type Ge(111) monochromator.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. Hydrogen atoms were positioned with idealized geometry (methyl H atoms allowed to rotate but not to tip) and were refined isotropically with U_iso(H) = 1.2 U_eq(C) (1.5 for methyl H atoms).

Table 3
Experimental details

Crystal data
Chemical formula	[ZnBr₂(C₆H₈N₂)₂]
M_r	333.33
Crystal system, space group	Trigonal, P3₁
Temperature (K)	220
a, c (Å)	7.3972 (3), 15.3874 (8)
V (Å³)	729.17 (7)
Z	3
Radiation type	Mo Kα
μ (mm⁻¹)	10.69
Crystal size (mm)	0.11 × 0.07 × 0.06

Data collection
Diffractometer	Stoe IPDS1
Absorption correction	Numerical (X-RED and X-SHAPE; Stoe, 2008 )
T_min, T_max	0.067, 0.156
No. of measured, independent and observed [I > 2σ(I)] reflections	7080, 2343, 2231
R_int	0.076
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.102, 1.06
No. of reflections	2343
No. of parameters	103
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.71, −0.73
Absolute structure	Flack x determined using 1049 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.01 (2)
Computer programs: X-AREA (Stoe, 2008), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), DIAMOND (Brandenburg, 1999 ) and XP in SHELXTL-PC (Sheldrick, 2008 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 2482737

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989025007613/nx2028sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989025007613/nx2028Isup2.hkl

checkCIF report

Computing details top

catena-Poly[[dibromidozinc(II)]-µ-2,3-dimethylpyrazine-κ²N¹:N⁴] top

Crystal data top

[ZnBr₂(C₆H₈N₂)₂]	D_x = 2.277 Mg m⁻³
M_r = 333.33	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P3₁	Cell parameters from 7962 reflections
a = 7.3972 (3) Å	θ = 10.4–27.1°
c = 15.3874 (8) Å	µ = 10.69 mm⁻¹
V = 729.17 (7) Å³	T = 220 K
Z = 3	Block, light yellow
F(000) = 474	0.11 × 0.07 × 0.06 mm

Data collection top

Stoe IPDS-1 diffractometer	2231 reflections with I > 2σ(I)
Phi scans	R_int = 0.076
Absorption correction: numerical (X-Red and X-Shape; Stoe, 2008)	θ_max = 28.0°, θ_min = 3.2°
T_min = 0.067, T_max = 0.156	h = −9→9
7080 measured reflections	k = −9→9
2343 independent reflections	l = −20→20

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0647P)² + 0.5878P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.040	(Δ/σ)_max < 0.001
wR(F²) = 0.102	Δρ_max = 0.71 e Å⁻³
S = 1.06	Δρ_min = −0.73 e Å⁻³
2343 reflections	Extinction correction: SHELXL-2016/6 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
103 parameters	Extinction coefficient: 0.043 (4)
1 restraint	Absolute structure: Flack x determined using 1049 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Hydrogen site location: inferred from neighbouring sites	Absolute structure parameter: 0.01 (2)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Zn1	1.06358 (14)	0.65633 (14)	0.01689 (5)	0.0206 (3)
Br1	1.31606 (14)	0.58557 (16)	0.07229 (6)	0.0339 (3)
Br2	1.18263 (16)	1.01071 (14)	−0.01098 (6)	0.0364 (3)
N1	0.8300 (11)	0.5540 (10)	0.1140 (4)	0.0214 (13)
C1	0.7097 (13)	0.3550 (13)	0.1380 (5)	0.0218 (14)
C2	0.5591 (13)	0.3036 (12)	0.2051 (5)	0.0209 (14)
N2	0.5454 (10)	0.4553 (11)	0.2470 (4)	0.0203 (12)
C3	0.6710 (12)	0.6539 (12)	0.2219 (5)	0.0217 (14)
H3	0.662006	0.761430	0.250495	0.026*
C4	0.8122 (13)	0.7038 (12)	0.1554 (5)	0.0222 (15)
H4	0.896891	0.844010	0.138842	0.027*
C5	0.7352 (15)	0.1869 (14)	0.0961 (6)	0.0286 (17)
H5A	0.644589	0.133729	0.045754	0.043*
H5B	0.698387	0.074531	0.137308	0.043*
H5C	0.879174	0.243448	0.078088	0.043*
C6	0.4191 (16)	0.0817 (14)	0.2324 (7)	0.0322 (19)
H6A	0.502059	0.028064	0.258741	0.048*
H6B	0.346705	−0.002001	0.181996	0.048*
H6C	0.317974	0.075293	0.274258	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0210 (4)	0.0201 (4)	0.0207 (4)	0.0102 (3)	−0.0004 (3)	−0.0012 (3)
Br1	0.0299 (4)	0.0399 (5)	0.0389 (5)	0.0228 (4)	−0.0114 (4)	−0.0094 (4)
Br2	0.0393 (5)	0.0218 (4)	0.0445 (6)	0.0126 (4)	0.0007 (4)	0.0070 (4)
N1	0.022 (3)	0.025 (3)	0.020 (3)	0.014 (3)	0.001 (2)	−0.001 (3)
C1	0.023 (4)	0.023 (3)	0.020 (3)	0.012 (3)	0.002 (3)	0.000 (3)
C2	0.023 (3)	0.018 (3)	0.022 (3)	0.010 (3)	−0.002 (3)	0.002 (3)
N2	0.020 (3)	0.022 (3)	0.017 (3)	0.009 (3)	0.003 (2)	0.000 (2)
C3	0.022 (3)	0.018 (3)	0.025 (3)	0.010 (3)	0.003 (3)	0.001 (3)
C4	0.024 (3)	0.016 (3)	0.025 (4)	0.008 (3)	0.003 (3)	0.000 (3)
C5	0.037 (4)	0.024 (4)	0.028 (4)	0.018 (3)	0.008 (4)	0.002 (3)
C6	0.037 (5)	0.022 (4)	0.033 (4)	0.011 (3)	0.011 (4)	0.005 (3)

Geometric parameters (Å, º) top

Zn1—N2ⁱ	2.085 (6)	N2—C3	1.344 (10)
Zn1—N1	2.118 (7)	C3—C4	1.374 (11)
Zn1—Br1	2.3380 (12)	C3—H3	0.9400
Zn1—Br2	2.3501 (12)	C4—H4	0.9400
N1—C1	1.336 (10)	C5—H5A	0.9700
N1—C4	1.340 (10)	C5—H5B	0.9700
C1—C2	1.424 (12)	C5—H5C	0.9700
C1—C5	1.494 (11)	C6—H6A	0.9700
C2—N2	1.341 (11)	C6—H6B	0.9700
C2—C6	1.498 (11)	C6—H6C	0.9700

N2ⁱ—Zn1—N1	103.1 (3)	N2—C3—C4	121.6 (7)
N2ⁱ—Zn1—Br1	109.2 (2)	N2—C3—H3	119.2
N1—Zn1—Br1	105.25 (19)	C4—C3—H3	119.2
N2ⁱ—Zn1—Br2	115.18 (19)	N1—C4—C3	120.5 (7)
N1—Zn1—Br2	108.13 (19)	N1—C4—H4	119.8
Br1—Zn1—Br2	114.87 (5)	C3—C4—H4	119.8
C1—N1—C4	119.5 (7)	C1—C5—H5A	109.5
C1—N1—Zn1	124.3 (5)	C1—C5—H5B	109.5
C4—N1—Zn1	116.1 (5)	H5A—C5—H5B	109.5
N1—C1—C2	119.7 (7)	C1—C5—H5C	109.5
N1—C1—C5	120.4 (7)	H5A—C5—H5C	109.5
C2—C1—C5	119.9 (7)	H5B—C5—H5C	109.5
N2—C2—C1	120.1 (7)	C2—C6—H6A	109.5
N2—C2—C6	118.8 (7)	C2—C6—H6B	109.5
C1—C2—C6	121.1 (7)	H6A—C6—H6B	109.5
C2—N2—C3	118.5 (7)	C2—C6—H6C	109.5
C2—N2—Zn1ⁱⁱ	124.8 (5)	H6A—C6—H6C	109.5
C3—N2—Zn1ⁱⁱ	116.7 (5)	H6B—C6—H6C	109.5

C4—N1—C1—C2	2.2 (11)	C6—C2—N2—C3	−179.8 (8)
Zn1—N1—C1—C2	179.1 (6)	C1—C2—N2—Zn1ⁱⁱ	−177.0 (6)
C4—N1—C1—C5	−176.6 (8)	C6—C2—N2—Zn1ⁱⁱ	0.8 (11)
Zn1—N1—C1—C5	0.3 (11)	C2—N2—C3—C4	−0.5 (12)
N1—C1—C2—N2	−3.3 (12)	Zn1ⁱⁱ—N2—C3—C4	179.0 (6)
C5—C1—C2—N2	175.4 (8)	C1—N1—C4—C3	−0.2 (12)
N1—C1—C2—C6	178.9 (8)	Zn1—N1—C4—C3	−177.4 (6)
C5—C1—C2—C6	−2.3 (12)	N2—C3—C4—N1	−0.7 (13)
C1—C2—N2—C3	2.4 (12)

Symmetry codes: (i) −x+y+1, −x+1, z−1/3; (ii) −y+1, x−y, z+1/3.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Br1ⁱⁱ	0.94	2.95	3.604 (8)	128
C3—H3···Br2ⁱⁱⁱ	0.94	2.99	3.687 (8)	132
C4—H4···Br2	0.94	2.95	3.605 (8)	128
C5—H5C···Br1	0.97	2.95	3.824 (10)	151
C6—H6A···Br1^iv	0.97	2.99	3.710 (10)	132
C6—H6C···Br2ⁱⁱ	0.97	2.95	3.820 (10)	150

Symmetry codes: (ii) −y+1, x−y, z+1/3; (iii) −y+2, x−y+1, z+1/3; (iv) −y+1, x−y−1, z+1/3.

Acknowledgements

Financial support by the State of Schleswig-Holstein is gratefully acknowledged.

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